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This chapter examines four episodes of The Simpsons, paying particular interest to one, The Days of Wine and D’oh’ses to connect the notion of pastiche with a symbolic interactionist view of media representation. We use The Simpsons and episodes pertinent to alcoholism and alcoholic imbibing to show that pastiche, which does not deny the resolute qualities of a serious social issue, nevertheless provides ironic and fantastic imagery to merge the serious and even tragic with the comedic. We use the four episodes to depict alcoholism as a disease but also as focal point for humor, making the contrast between The Days of Wine and D’oh’ses and its classic alcoholism-film counterpart, The Days of Wine and Roses, central to the tragic-comedic connection. We further draw upon Denzin’s notions of the comedic drunk and the alcoholism alibi to discuss how pastiche both inspires attention to alcoholism as a serious medical disease and disease of the self and to alcoholism as pivotal to comedic character development and the emergence of pragmatic and creative selves.